Finding cheap flights

My friends and family know that I’m into travel.  They also know that I like to save money.  So a question I regularly get is how to find cheap airline tickets.

My first recommendation is to save up points and miles to fly for free, but let’s face it, unless you’ve planned far in advance, that may not be a possibility for an upcoming trip.

So what about when you have to buy airline tickets?  Which website to use?  When to buy?  How to save?

I wish there were a great answer that applied across the board.  There definitely is not.  But there are some ways that can help you save.


When to buy

Is there an optimal time to buy your tickets before your trip?  In general, the standard is 5 months before and international trip and 6-8 weeks before a domestic trip.  I guess the airlines figure those who are planning farther ahead than that will be happy to be taken for a ride?  Maybe a little bit.  Or maybe it’s just that they haven’t gotten around to managing their revenue on flights that far out, since they’ve still got time to fill the seats.  In any case, those timelines are the guidance that I share, and it’s worked out pretty well in the past.  Of course there may be surprises, such as when you buy your tickets on Monday (exactly 3 months before your trip to New York), and then just for fun on Wednesday, you check to see if the price has gone up–and it’s actually gone down by $75 per person.  ACK!  Yes, it happens, unfortunately.  Or the other case when you are getting ready to buy your tickets on Monday, and by Tuesday when you visit the site, they’ve gone up by as much.  Always a bummer, but it’s definitely a bit of roulette when buying tickets and trying to get the right price.

Kayak Price Trend

Kayak’s “Price Trend” feature lets you know what prices on a given itinerary have done recently, and whether the price is expected to rise or fall in the next 7 days

There used to be a pretty cool tool/website called Farecast, which would tell you whether it expected ticket prices on a given itinerary to go up or down in the near future.  It was bought by Microsoft and was recently decommissioned.  Fortunately, about a year ago, Kayak released a similar capability, which allows you to see what the price is expected to do in the next 7 days.  It’s not a guarantee, but it will let you know whether the algorithms expect prices to rise or fall in the coming week–whether to “WAIT” or “BUY”–plus a little graph showing what the price for this itinerary has done over the past 90 days.

As for specific days of the week recommended for buying tickets–historically, the trends said Wednesday afternoon, but in recent years, the difference between Wednesday and other days of the week has diminished.  In some cases, destinations attempting to attract both leisure and business travelers will see lower ticket prices listed on weekends, when leisure travelers are more likely to buy.  To be honest, I’ve almost never seen a day-of-the-week appreciable difference in ticket shopping, so don’t focus too much on that.


Where to buy

There are lots of options these days for buying airfare, but here are the three main buckets:

There are pros and cons to each, so here’s my summary of the three buckets.

CategoryOnline Travel AgenciesOnline AggregatorsAirline Websites
Google Flights
AboutOnline Travel Agencies more or less took the place of travel agencies. They buy tickets from the airlines and sell to the public.Online Aggregators crawl the Internet in search for the best fares from a variety of sources, including the Online Travel Agencies and the Airline Websites.These are the websites owned and managed by the airlines, themselves.

The ability to book package deals such as flight+hotel, which in many cases offer a great deal

The four I’ve mentioned here are reputable and experienced–you’re unlikely to run into problems (although see cons below…)

In general, these will find the best price available.

The user interfaces on these (especially Hipmunk) are generally the most friendly for finding the flights you want. Hipmunk pretty much blows it out of the park in this regard.

There’s less irrelevant info to wade through if you already know which airline you want.

You’re dealing directly with the airline, just in case anything goes wrong.

You can pick your seats at the same time that you book your ticket.

You can more easily take a look at award seat availability if you need to.

You’ll easily get any frequent flyer priveleges to which you’re entitled.


If anything goes wrong with your flight, there’s a slight risk of finger-pointing between these OTAs and the airlines. But this has improved over the years.

In most cases, you’ll still need to visit the airline website to choose seats or otherwise manage your itinerary.

You don’t actually book with any of these guys, so you’ll have more clicks and visits to other sites (such as the other two columns in this table)

You may not get the best price (although in today’s data-driven, connected world, this is becoming less of an issue).

You can’t see your full array of options (from other airlines).


From a quick glance at the table, and the number of pros and cons for each, you might think the airline websites are best. But really, each one is good for its own thing.


I admit, I love hipmunk.

If I’m beginning a flight search and I’m wide open to the various options, I will almost always start with Hipmunk.  I love the site.  It’s graphical, makes it easy to see the options, the airlines, the layover, the timing–and even the “agony”–a calculation of layovers, flight times, and price.  There are even some advanced options that you can play around with that have come in very handy.

If I already know the flights/airline that I want, then I’ll generally start on that airline’s website.  Not only can I get right to it–I can also check award availability and see if I can get my ticket with miles instead of dollars.  Always a plus.

If I’m looking for a vacation package (including flights and car rental/hotel), I’ll usually start with one of the Online Travel Agencies.

If I’m only buying an airline ticket (i.e. no hotel/rental car), the prices vary little across the different options, in my experience.  We live in a world where real-time data availability is a reality, making price differences less and less noticeable across the various portals.  When it all comes down to it, if the price differential is within $5-10/ticket, I will almost always choose the airline website, since there’s the least likelihood for shift-the-blame finger-pointing if something goes wrong at some point, and I have confidence that I’ll receive any benefits that are due, either credit card or frequent flyer benefits.  But if the differential is more than that, I’ll go with one of the third parties, and things generally work out just fine.


A note about award tickets

I just wanted to add a little note that most of this advice is irrelevant when it comes to award tickets (i.e. redeeming points/miles for free tickets).  In the case of using airline miles to book an award ticket, generally the sooner you book, the better (most award seats open up 11 months before the scheduled flight).

The one exception is when you use a fixed-value point program, like BarclayCard Arrival Plus or Southwest Rapid Rewards.  In such cases, you’re booking tickets (with points) based on the dollar price of the ticket, so the above tips that will help you find a lower-priced ticket should apply.

Remember, if you’re tired of paying dollars for airline tickets, it’s never too late to start finding ways to save up points and miles for lower cost travel!

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  1. […] getting serious about it until September.  While 3-5 months is a perfectly appropriate time to buy tickets with dollars, when you use miles you’re really best off getting them as soon as your travel dates are firm, up […]

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